Where should I go? Meet the destination checklist

Points junkies play a fun game called “chase the fare”. If you’re not familiar, when some crazy low airfare comes up, you don’t think, you just book…and then figure out what you will do when you get there! It’s why you’ll see bunches of folks on twitter going to and from places like Bahrain within a short period of time.

To the average traveler, it’s just a weird way to spend your precious two weeks vacation a year. I get that. You probably have your “top five” in mind. Let me guess: Paris, London, Rome, Hawaii, Australia. Am I close? Twenty years of close to full time travel and you pretty much figure out what people dream of.

Now let me ask you a question: Why (Paris, London, Rome, Hawaii, Australia)? Can you really give an answer that doesn’t come out of a rom-com? Here’s where I ask you to take a page from the fare chasers. I don’t want you to go quite as far down the road to the loony bin as many of the FTers I’ve met (and I say that with love:), but one thing they’ve got right is flexibility.

When you think about your next trip, I want you to think about the experience you want first, then choose a destination.

I use a checklist like this one:

Do I want an active trip or a restful one?
Urban, Rural, or a mix?
One destination or moving around?
Luxury or simplicity?
1st World or 3rd?
Am I limited by the calendar?
By the climate or the seasons?
What is my cash budget?
What is miles/points budget?
Are there any sweet spots in my miles/points programs that fit the above criteria?
What about other promotions? (Skyauction, Luxury Link, EVR, etc.)

An example:

Two years ago my family of 4 spent two weeks in August hiking volcanoes, ziplining and hiking on coffee plantations, eating tropical fruits, boat touring, and enjoying the Pacific on black sand beaches. The total all in cost for airfare, food, private tours and a two bedroom gorgeous condo in town in an upscale hotel with a pool, gardens and activities? $2500. No miles or points involved. Hawaii? No. Guatemala.

I’m not going to tell you that going to Guatemala is exactly like going to Hawaii. For one thing there aren’t any Mayan temples in Hawaii;) But by focusing on the experiences first, I was able to create a jam packed trip that fit our family for a lot less.

Using the same method for my 2014 solo trip, I finally narrowed down my list as such:

Do I want an active trip or a restful one? mix
Urban, Rural, or a mix? mix
One destination or moving around? moving around, but within a limited area.
Luxury or simplicity? flex
1st World or 3rd? 1st, 3rd only if luxury hotel
Am I limited by the calendar? very! Must be August 3-16.
By the climate or the seasons? Yes! Dates make much of South America in Winter. Much of Asia in Monsoon. Much of Carribean/Mexico/Central America in Hurricane.

This was a good point for at least a partial decision…Europe it is! I went ahead a booked an open jaw award ticket.

What is my cash budget? Like to be under 1K
What is miles/points budget? 300k Club Carlson (+Visa), 4 free Marriott Nights (up to Cat 5), 50k Hyatt, 50k Starwood (+AMEX)
Are there any sweet spots in my miles/points programs that fit the above criteria? Lots of Cat 2-3 SPG in Italy, Marriott Cat 5 resort in Tuscany, Lots of Club Carlson in Italy, BA (Avios) flies to 20 destinations in Italy
What about other promotions? (Skyauction, Luxury Link, EVR, etc.) Lots of Luxury Link in Italy

Winner Winner chicken dinner!

So now that I’ve chosen Italy, I’ll just have to keep an eye out for promos and narrow down a region. Suggestions welcome!

Original publish date: Nov. 13, 2013. I’ve returned to this checklist over and over again.